生物発光分子系を基盤とする機能性色素化学 : イミダゾピラジノンπ電子系の基礎化学と応用 [in Japanese] Functional Dye Chemistry Based on Bioluminescence-related Molecules : Fundamental Chemistry and Application of the Imidazopyrazinone π-System [in Japanese]
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The imidazo [1, 2-<I>a</I>] pyrazin-3 (7<I>H</I>) -one (imidazopyrazinone) ring is a core structure of the luminescent substrates isolated from marine bioluminescent organisms, such as the crustacean <I>Vargula</I> (<I>Cypridina</I>) and the jellyfish <I>Aequorea</I>. To develop the bioluminescence chemistry, we revealed the unique π-electronic character of the imidazopyrazinone ring system on the basis of the pioneering study by Goto et al. In this article, we provide an overview of the fundamental chemistry of imidazopyrazinone including the molecular structure, aromaticity of the π-system, molecular orbital, solvatochromism, acid-base behavior, tautomerism, and electron-donating ability. Especially, the imidazopyrazinone π-system having a twitterionic character is sensitively affected by a microenvironment around molecules, to show a continuous absorption-spectral change. Therefore, imidazopyrazinones are useful as functional dyes to indicate a magnitude of an interaction with a microenvironment, such as a hydrogen bond and a Lewis acid-base interaction. We also describe applications of imidazopyrazinone derivatives as indicators for naked eye detection of the hydrogen-bond donor strength of a solvent molecule, the Lewis acidity of a metal ion, and a hydrophobic interaction with a protein.
- J. Synth. Org. Chem. Jpn.
J. Synth. Org. Chem. Jpn. 64(10), 1062-1072, 2006-10-01
The Society of Synthetic Organic Chemistry, Japan